Ready as I was ever going to be, I ordered him to the bedroom where I met him with a long kiss. I gripped the riding crop in my right hand and roughly grabbed the cage encasing his cock with my left. I whispered in his ear:
“Are you ready to play, my slutty little slave? Is that dribbly dick of yours aching for me?”
I pushed him face down over the end of the bed, the wooden frame hard against his belly.
With the crop I traced the lines of his body, starting at his shoulders and working my way down the length of his torso, his arse to his thighs.
“Spread those legs apart slave,” tapping the crop against his calves. He widened his stance and leaned lower over the bed. His face was pushed into the covers, his hands gripping the slippery fabric.
“Look at you, with that arse in the air,” I went on. “So needy, so undeserving of mistress.”
“I think you want me to punish you, don’t you slut? You want me to hurt you for disobeying me today.”
“Oh yes mistress.”
“I can’t hear you.”
I ran the crop between his arse, spreading his cheeks with its braided shaft. He was still wearing his sissy g-string.
“This is a very silly little g-string isn’t it, slave?”
“Holding your pathetic little dribbly dick, leaking everywhere.” I brought the end of the crop down on his arse. “I think you like the feel of that.” Across his shoulders. “You like being punished by your mistress.” I tapped the crop aggressively but not painfully along the length of his arms. He wriggled impatiently.
“Stop wriggling sissy boy. Do you have a problem being still?”
“No mistress,” as his body betrayed him by wiggling some more. His fingers open and closed around bunches of the bed cover.
I leaned my body against his, forcing his face back down into the bed. I reached out and squeezed his nipple between my fingers. A soft exhalation, a groan.
As I righted myself, I smacked his arse with my open hand and his body recoiled from the impact. I caressed the blow and squatted behind him. With my tongue, I traced circles on his arse cheeks, kissed it gently on one cheek then the other. I smacked him again.
“Look at this needy arse … I think it wants to be fucked.”
“Oh yes mistress.”
“But not yet, no, first I need to play with it.”
From the floor behind me I picked up a tube of lube and a vibrating egg with a tail for easy removal. I generously applied lube to my fingers and his tight hole, slipping in the tip of my finger. He groaned.
“Oh, you like that, don’t you, sissy boy?”
He nodded into the bed.
“I can’t hear you slave!”
I slid my finger in a little deep and switched on the vibrating egg. I pressed it against my finger, still in his arse.
“Oh fuck!” he exhaled, squirming into and against the vibrations.
I moved the egg lower, to his dribbling cock, hard and angry in its cage. The vibrations resonated against the metal. His breath caught and he gyrated his arse trying to control the direction of the sensations. I passed the egg over his balls, the taut skin of his perineum and back up to his tight slippery hole.
I tormented him, alternating pushing my finger and the egg into the small opening. With my free hand, I squeezed lube onto the shaft of the dildo I was wearing. It also vibrated, but he didn’t know that yet.
“How does that feel my little slut?
“Good mistress. Really good.”
“Are you ready for me to fuck that sissy hole of yours?”
“Yes please, mistress.”
I left the egg quivering inside his g-string, and playfully slid the end of the lubed strap on up and down between his arse cheeks.
“Can you feel that slut? I’m going to fuck you with this big dick and there’s nothing you can do about it.”
I felt more than saw him brace himself, he regathered the bed covers into his hands, adjusted the position of his feet, and kept his arse high in the air. In my heels, I was the perfect height to fuck him and, with much fumbling on my part, the length of the dildo slid inside him.
I let him push himself onto it, more than I helped in any way. I find it unreasonably awkward to fuck with a strap on. Without the benefit of being able to “feel” my way in, I needed him to guide the dildo’s entry but finally we got there. We began to move in rhythm, and I could feel my own excitement building. I almost forgot to press the button to start the vibrations.
“Oh wow!” he exclaimed appreciatively as I endeavoured to ignore the screaming of my calves. Perfect height I might be, but it had been far too long since I’d worn anything higher than a pair of runners and my legs were crying their displeasure.
I desperately wanted to keep going but my stamina was weakening as pain took over and I had to call a stop so I could kick off the stupid heels. Deprived of their five inches, I had little chance of fucking him in the current position being that I was only 162cm tall. We fumbled and he tried to instruct me for a few minutes, but my confidence was fading.
“I think we need to switch positions,” I admitted in defeat.
Off the bed, he reached for me and I let him pull me in close. We kissed deeply and he pushed me down on the bed. Wait a minute, this wasn’t how it was supposed to go?
The strap on dildo was still vibrating furiously between my legs and he put all his weight on me, grinding the dildo against my clit. Now it was my turn to squirm as he triumphed over me. I was a wet and sweaty mess when I finally came to his gentle whispering telling me to let go. But he was still locked in his cage and I desperately wanted to feel him inside me.
“Would you like me to release you, slave?”
“Yes, please my mistress.”
Fortunately, the key was in easy reach and I slipped it into the tiny padlock with more confidence than I felt. However, when it came to pull the cage off, I shied away. Having never used one before, I had no idea what pulling it off was going to do as I couldn’t easily see how it had attached in the first place. I let him show me and gently pulled it away from the cock ring it attached to.
Seated on me, I played with his swelling cock while he ground the still vibrating dildo attached to me. It had slipped sideways in the harness and we shared one of those moments where you had to laugh at the ridiculousness of the scene.
I told him I still wanted to fuck his arse and ordered him to slide back down on the dildo, now righted. With some more generous lashings of lube, he eased it in and began to rock in time to my thrusting. I masturbated his cock while he leaned back into the dildo up his arse, watching his face for the tell-tale signs he was going to come.
He’d been waiting so long for this release, built up all day and the night before from our sexting. His cock caged for most of the day was finally free to spill a big thick load. I wanted this for him, for us. I wanted to hear him explode.
When he came, my purple vibrating dildo was hidden in his arse and the collar was askew around his neck. But when he collapsed on top of me, I felt like a fraud, like I’d let him down somehow. He immediately assured me that wasn’t the case but like an itch that can’t be scratched, it gnawed at me.
It was only later I realised how vulnerable we were both were in this, how much trust he placed in me and the week before, that I had placed in him. It wasn’t like me to be this open, with anyone. Fuck knows my ex had tried. I’d shutdown his overtures and recoiled like a frightened snail. My first line of defence had always been to throw up walls. And now I felt exposed, exposed with a strap on dick. I’d love to hear the psycho-analysis on that one.